Are my sentences correct?

Can you tell me if I am correct in these please?

1 How long is shipping?
How long does shipping take?

This is confusing but I think 2a you would say Is this the road that your road is off of where you go up the hill to your house? and 2b Is this the road where we turn and go up a hill to your house?
The sentences might not be 100% correct.

2a If you are on a road that leads to your road, how would you say the following?
Is this the road where we turn and go up a hill to your house? Is this the road that your road is off of where you go up the hill to your house?

2b If you're road is coming up, how would you say it?
Is this the road where we turn and go up a hill to your house? Is this the road that your road is off of where you go up the hill to your house?


I heard an English person say:

3 How successful do you think you'll be to capture him? Is it incorrect?


Is this explained well?

4 Is this sentence correct? Is it understood? How do I explain that if you go against the grain on velvet blanket you can make a mark?

She lay on her bed drawing with her finger on the velvet blanket and erasing it with her palm as if the blanket were a magic board.
I like playing with the velvet fabric. When moving the velvet against the grain it leaves a darker trace as if you were drawing on it and than erasing it by going with the grain like a magic board.

Does this make sense to you? Is it correct?

5 When I hear people say they are born in 92, it seems so young to me because to me 92 means they are like 15 but they aren't they are 21. That hits me with perspective on my own age.

Thank you so much